Dichloroacetyl chloride → HCID 46916410, compound

HRID 2045928Notes

Reaction equation

HRID 2045928 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.CCN(C(C)C)C(C)C.[Cl:27]C(Cl)C(Cl)=O.[CH2:33]1C[O:36][CH2:35][CH2:34]1>C(OCC)(=O)C>[Cl:27][CH2:33][CH2:34][C:35]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[O:36]

Participants

6

Reactant 4

HCID 6593Dichloroacetyl chlorideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 46916410HCID 46916410, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (128 mg, 0.578 mmol) and DIEA (115 μL, 0.694 mmol) in THF (5 mL), dichloroacetyl chloride (61 μL, 0.636 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 48 hrs, diluted with ethyl acetate (20 mL). The organic phase was washed with water (10 mL) and then brine (10 mL), dried over MgSO4, and the solvent was evaporated in vacuo to afford a light-yellow solid. The solid was triturated with Et2O, filtered, and submitted to preparative LCMS to afford 3-chloro-N-[3-(quinoxalin-2-yl)phenyl]propanamide (50 mg, 28% yield). LCMS calculated for C17H14ClN3O (M+H): 312.08. found 312.14. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.30 (1H, br. s), 9.50 (1H, s), 8.52 (1H, m), 6.65-8.60 (2H, m), 8.58 (1H, d, J=7 Hz), 7.95-7.84 (3H, m), 7.55 (1H, m), 3.91 (2H, t, J=7.1 Hz), 2.88 (2H, t, J=7.1 Hz).

Workup

  1. washThe organic phase was washed with water (10 mL)
  2. dry with materialbrine (10 mL), dried over MgSO4
  3. customthe solvent was evaporated in vacuo
  4. customto afford a light-yellow solid
  5. customThe solid was triturated with Et2O
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ea76fa0699914c28998670c1565db79d
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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